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Somehow, I just now noticed this thread... I initially considered just adding my 2 cents without reading through all of the posts, but I decided that I would and I'm glad I did. There's been a lot of good advice offered by everyone here that considers many different reasons, scenarios, solutions, outcomes, etc.
The simple fact is that there doesn't really seem to be a definitive solution here, seeing as how he's the only one who can really shed light on the best way to approach things and he's not talking.
Getting advice from others on here is great - not just because it's given you ideas on how to approach him about it, but it's also given you a ton of insight into the actual act of dressing and I think you've come to realize that you'd have to cast a very wide net to capture the many different ways that dressing plays a part on people's lives.
I'll start off by saying a couple of things that may come across as harsh or dismissive, and others have already touched on it, but I think it deserves to be repeated and considered.... You're both still very young. If I remember correctly, I believe you said that he's 24 and you're 21- you also stated that you've been together for 4 years... I'm certainly not trying to sabotage your relationship and I'm not trying to be cynical, so please don't think that I'm just claiming that it's doomed no matter what and you should just throw in the towel. Reading through this thread, I can honestly say that I feel like I have been in the same position both of you are in right now. In terms of how you feel on your end- I can tell you that I remember a girl I was in a serious relationship with where I always felt like I was actually fighting with a her so to STAY with her. It happens all the time with relationships everywhere, but when you stop and really think about it, it's actually a completely ludicrous concept. I know that when you're in the relationship and in that moment, it's VERY hard to see. If it doesn't work out, trust me... There will be a day when you look back and realize that you gave him way too much credit, way too much power, way too much energy, and way too much time. Hopefully, you can work it out, but if not, just don't waste anymore time than you have to. That's usually when it gets to the point that there's nothing left but regret and resentment and things just end badly all around.
Once again, please don't think that I'm being a pessimist... I'm all in favor of finding the right woman and making it last. I've dreamed of nothing else and I'll never stop trying to find it. It's just that I remember a relationship I was in that was very much like yours except that it was me trying to fight for her. My dressing wasn't even an issue as I was in a very long period where I somehow completely lost the desire to dress and she had no idea I had ever even done it before. I didn't stop out of shame, guilt, fear, etc. I just simply woke up one day and other things were more important. Still, I was the one trying to fight for her but she could care less... She was secretive, dismissive, insensitive, hateful, etc... Looking back, I'm so glad I didn't waste any more time or energy on her.
Now in terms of him, I really felt many connections with the way you described him. I'm described by friends and family as funny, sports junkie, guys guy, etc... However, I do CD. I keep it a very close secret and I'm very discreet. My situation is different as my dressing is really just a fetish. It's for my own sexual gratification. I don't have any doubts about my gender, sexuality, etc. Although I don't know anymore about him that what you've indicated, I think he may be like me where it's just a fetish. Of course, none of us know this for sure, but I think if it were anything else, you might have spotted some signs.
Like him, I remember the countless times when I've sneaked panties or lingerie from the women I've dated... I remember the way I would lock the door and check it countless times when I was wearing any femme clothes and how I would scramble to strip off the panties and stash them out of sight and throw on a t shirt and some sweatpants as quickly as I could when there was a knock on the door...trying not to arouse suspicion. I remember when I was around 11 or so, I had a few pairs of panties I had managed to scrounge up and I was so scared of my family finding them, that I eventually resorted to wrapping them up in some garbage bags and stashing them deep in the woods about a mile away from my house. Eventually, I grew to realize that was a little too far and I located a secure place in my room to hide them. Still, I remember how carefully i hid them and the unbelievably absurd lengths I would go to to hide my dressing from others. I would lock the door and check it multiple times... I would make sure that the curtains were pulled completely shut where nobody could see in... I would turn off the A/C or heater so that I would hear if their car pulled in the driveway earlier than usual. Some of these things seems completely ridiculous but I can still remember the unbelievable fear of being caught. For some, it may have been easier than others, but I cannot stress how ABSOLUTELY TERRIFYING the idea if being discovered was to me. I can honestly say that if anyone had discovered my secret back then that I mostly likely would've taken my own life. It wasn't that my family were intolerant, evil people... Far from it... I wasn't mentally ill or abused... I was, however, a very self-conscious and very insecure kid and teenager. And like him, I also battled anxiety, stress, depression, etc. his may be because of his dressing, but IMO, it sounds like he's got some more things bugging him than just the dressing.
Like some have said and you already know, his denying his dressing even when faced with undeniable proof is completely ridiculous. However, I do think it shows how completely terrified he is about anyone discovering his "secret". That's also why it's a good thing that you didn't make any rash decisions about confronting him or avoiding him and the manner in which you would do it. In all honesty, you know him better than anyone. Many on here, including myself, would love to find a woman that's so supportive and understanding as you've been about this. That being said, it sounds like he pretty lousy at communication in general. You could go in with kid gloves or guns blazing and I still couldn't tell you how he'd respond to it. Flip a coin?
Also, as far as the dating app goes, you know if he's shown behavior that's associated with cheating. I personally think that if he were cheating, that he would've just posted pics of himself NOT dressed on there. I can tell you that the Internet is an amazing place of safe expression for a closet CD that is hellbent on keeping his secret, but also cannot fight the desire to be seen.
As I stated, my dressing is a fetish, - while I won't get into specifics as that's not the issue, I will say that for me , it's a combination of factors that excite me when it comes to dressing- shiny fabrics, platform boots and heels, kinky lingerie, massive breast forms, heavy makeup, etc. while I love all of those things, I also love that it's SO far removed from my regular, normal life. Knowing that, I can also say that it's also the fact that it's so taboo and "naughty" that drives my desire to dress. Obviously, I won't go out and interact with the public dressed like this, so posting pics online is a way that I express myself. Regardless of what anyone on here says, the first time you post pics of yourself dressed online, it is a thrilling rush. I know he hid his face - I do the same- Even if the vast majority of responses and attention that I get online are from men, and even if its completely anonymous, it's still an incredibly euphoric feeling to put yourself out there and be exposed. If I had to bet on whether it was actual cheating or just getting a thrill from having people see his pics online, I'd feel pretty confident it was the latter. Still, when you're dealing with the fact that it's a dating/hookup site and he's so completely dismissive about it, you have to address that because it's important to protect yourself no matter how confident you feel that he's been faithful to you.
As far as why he didn't make more of an effort to conceal the background in the pics and hide his personal effects and belongings out of sight, I'm guessing it can be chalked up to that being the first time he's done it and that this is a lesson he's now learned. I'm sure he was extremely excited and was getting an exciting rush from posting pics of himself online dresse in women's clothing. He rushed through in the excitement and simply forgot. Nothing more. From now on, he will take the extra steps and all pics will be done with no indications of anything that could be tied to him. It also tells me that he really didn't think that you would look for him doing that. If I were cheating and trying to hide it from my girlfriend, I would take any and all precautions I could to conceal my identity. Neither of which really says anything good about your relationship.
Which ties into the last thing I'll mention... He seems to have VERY little respect for you. I think that the word "respect" has lost part of its meaning with too many people in this world. It seems like whenever anyone mentions "respect" far too many people automatically get an image of a gangsta rapper "demanding respect" or a cast member from Mob Wives telling some skank to "respect" her... Yes, those are examples of respect, but it also ties in with both you and your relationship... And He seems to have very little "respect" for both. Regardless of how you feel about him, how long you've been together, your desire to "not give up", you worrying about what he's going through, etc... None of that changes the fact that he has been very cavalier with your feelings and the relationship. He doesn't appear at all afraid of losing you and he doesn't feel at all concerned about doing anything to patch things up. He's indifferent about your desire not just stabilize, but improve the relationship. To me, it seems like he's just hoping you'll lose interest but he also might be hanging on because he so scared that you're going to out him to the world. I wonder if there would be anything at all between you two if you hadn't discovered all of these things? ... I think forcing the conversation is necessary to get answers, but given how he's acted so far, I think he's more than likely content to end the relationship as opposed to coming clean about ANY of the things you've discovered.